
Vacation rentals with a pool in Madison
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Madison
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

The Airy Aerie: Owners' Club access, golf nearby!
Welcome to the Airy Aerie: an avian themed townhome in the heart of the Galena Territory. Our space has been carefully curated to reflect the diversity of birds you will find in the natural surroundings of the area. There are two ensuite bedrooms and a full kitchen featuring granite countertops and stainless steel appliances. There is a loft space upstairs where a rollout twin bed can be set up. Our home can accommodate a maximum of 6 overnight guests (assuming 1 person on the twin rollout bed).

Spring Green River Pines
Spend a few days in the beautiful countryside. A private entrance to the lower level of home (completely separate from our home) that includes a central room, 2 bedrooms with kitchenette, & 1 lg bath. WiFi >500 Mbps speed. Smart 60" TV, Bluetooth Airplay/stream compatible. Parking on sight. Great location 5 min from beautiful downtown Spring Green. Close to APT, Taliesin/Frank Lloyd Wrights Home/School, House on the Rock, WI River, Gov. Dodge State Park and 1/2 hr to Devils Lake State Park.

Grace-Jo @ Tamarack Highland 5
Upgrade to our Noah's Ark package after booking! This home is a beautiful one-bedroom at the Tamarack and Mirror Lake Resort. We offer plenty of amenities to keep guests of all ages busy. Conveniently located near all of the attractions the Dells are known for. The condo is attractive, clean and includes a well-equipped kitchen, comfortable beds, and smart TV's for the rainy days. This property is great for a couple or a family and is near the included pools and activities at the resort.

Lake Geneva Retreat! Fireplace! WiFi!
Your cozy getaway begins in a newly redesigned condo with patio (there are stairs to get to villa), conveniently located between Lake Como and Lake Geneva in Interlaken Resort! Just a short peaceful walk to lake, restaurants, pool, tennis, volleyball, boat launch, small craft rentals, & more! The resort community is located by Lodge Geneva National, which adds additional restaurants and available amenities at an additional charge. Many local areas to explore & visit will await your arrival.

Private, Galena Log Cabin
This custom log cabin is the perfect getaway for friends & family seeking the solitude of the Galena Territory and fine dining and shops just 10 minutes away on Galena's Main Street. Each of the 3-levels offers an owner's suite with bath. Cozy up to 2 fireplaces, grill on the deck, or make 'smores at the firepit. The cabin has high speed, fiber internet and the lower-level walkout features a 55” flat screen TV. Guests can access swimming pools & pool tables at the Owner's Club 7 minutes away.

The Wanderlust at the Sunset Cove
Riverfront one bedroom condo in a tranquil area of Downtown Wisconsin Dells. Take a stroll near the beautiful River Walk and enjoy the magnificent scenery and unique attractions of Downtown Wisconsin Dells. Whether you need a few days to relax and decompress or if you are in town for business or games, our condo offers a fully equipped kitchen, a king size bed and a queen size pull out couch . There is an indoor community pool, hot tub and sauna. There is also a seasonal outdoor pool .

*Winter Fun* *Hot tub-Fire-3 king beds-Game room*
Relax, unwind, & explore at this winter retreat in Galena Territory! Escape to this cozy, spacious cabin for a peaceful winter getaway. Sip morning coffee as snow falls through the trees, then unwind in the hot tub or by the fireplace. Roast marshmallows around the fire or enjoy arcade games, air hockey, darts, and more indoors. Stay active with access to the owner's club—indoor pool, fitness center, and pickleball (8 amenity cards included). Perfect for relaxation and winter adventure!

Octagon treehouse Hottub-pool-fireplace-firepit
Unique "tree house" - an octagon tiny house, surrounded by the woods! 2 bedroom, 2 bathroom home you can enjoy the views of nature all around, with floor to ceiling windows. One king bed, one queen bed. Modern comforts with fun flash blacks. Private hot tub and firepit look into serene woods! Sit by the indoor gas fireplace and enjoy our record collection. Soak in a Japanese soaking tub. Enjoy fall colors or watch snow fall! Community indoor poor, seasonal outdoor pool, gym access

Hot Tub/$0 Cleaning Fee/Golf Course/The Hemlock
Our 4 bedroom, 2.5 bath home in downtown Spring Green, Home to Frank Lloyd Wright’s Taliesin, American Players Theater, the House on the Rock, and Tower Hill State Park, the vibrant village of Spring Green is a place where nature and art meet. Just 45 minutes from Madison, And the Dells Waterpark. Do You enjoy Golfing Or snow mobile Riding? Relax with the whole family at this peaceful place to stay. walk to downtown or the Rec Park with soft ball diamond and skate board Park.

Luxurious Chula Vista Retreat
No resort fees! Experience all the Wisconsin Dells has to offer while staying in this luxurious condo, located inside the action-packed Chula Vista Resort! Enjoy the resort's waterparks, restaurants, 18-hole golf course, zip line and so much more! Minutes from all of the area's attractions including Noah's Ark and hiking trails! Then relax in our Jacuzzi tub, cozy up to our two fireplaces, hang out in our spacious living room or cook a family meal in our full-size kitchen!

Serene Lakefront condo with magnificent view, pool
Welcome to this serene waterfront villa in Lake Geneva, Wisconsin, a haven for relaxation. This elegantly designed one-bedroom retreat is perfectly nestled on the shores of Lake Como, offering a blend of rustic charm and modern comfort. The real brick walls and cozy fireplace create a warm and inviting atmosphere, providing unforgettable memories in this beautiful Wisconsin setting. Local laws require all guests names and address be provided prior to check in.

★GLACIER CANYON RESORT WITH WATER-PARK AMENITIES★
Welcome to Wisconsin Dells and the city of Baraboo, a popular vacation playground best known for its beautiful river scenery, endless entertainment options and larger-than-life water parks. Inside the Wilderness Territory a theme park where family fun reign supreme is a top ranked indoor and outdoor water park. You can also find some excellent shopping, visit wineries for tastings, practice your swing on local golf courses, and win big at Ho-Chunk Casino.
Popular amenities for Madison rentals with a pool
House rentals with a pool

Hot tub | 3BD|3BA en-suites | Resort Amenities

The Tree House

Modern Home w/Amazing Views, Hot Tub, Game Room

Treehouse • Hot Tub + Fireplace • Serene Getaway

Stunning 5 bdm home on The General in Galena Terr!

Exec Retreat Heated Pool 7 Beds; 2.5 Bath 6000 sf

New/Fullyloaded/Golf sim/theater/Hot tub/Kingbeds

*Ski*Hot Tub* Firepit*Owners Club*Dog Friendly*
Condo rentals with a pool

Condo in Wisc Dells for 10-14 ppl

Comotose by the Lake

Chic Condo in Lake Geneva.

FUN-tana All Year Round Abbey Springs Fontana WI

*Pool/Hot Tub | 2 BR Condo | Waterfront | Downtown

Spacious 3BR Condo Retreat

Upper Dells River Walk [1BR]

Dells Lakefront Luxe - A Waterfront Property
Other vacation rentals with a pool

Cute and cozy 2 bedroom house perfectly located!

Fast Wi-Fi | EV Charger | Fireplace | Hot Tub

Modern Cabin with pool, hot tub and outdoor sauna

The Cottage on Lake Galena

Perfect Getaway: Newly Renovated

2 BR l 4 beds w/Game Room, Fire Pit & Star Gazing

Spacious Delightful 2 Bedroom Home

Sunset retreat oasis Pool hot tub river fishngame
When is the best time to visit Madison?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $120 CAD | $123 CAD | $130 CAD | $168 CAD | $164 CAD | $166 CAD | $175 CAD | $166 CAD | $166 CAD | $137 CAD | $124 CAD | $120 CAD |
| Avg. temp | -7 °C | -5 °C | 1 °C | 8 °C | 15 °C | 20 °C | 22 °C | 21 °C | 17 °C | 10 °C | 3 °C | -4 °C |
Quick stats about vacation rentals with a pool in Madison

Total vacation rentals
Explore 60 vacation rentals in Madison

Nightly prices starting at
Madison vacation rentals start at $28 CAD per night before taxes and fees

Verified guest reviews
Over 980 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wifi availability
60 of Madison vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Madison rentals

4.8 Average rating
Madison stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Madison’s top spots, include Henry Vilas Zoo, Wisconsin State Capitol, and Olbrich Botanical Gardens
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- Rentals with pools United States
- Devil's Lake State Park
- Mt. Olympus Water & Theme Parks
- Noah's Ark Waterpark
- Wisconsin State Capitol
- Mt. Olympus Parks, Outdoor Theme Park
- Lake Kegonsa State Park
- Mirror Lake State Park
- Yellowstone Lake State Park
- Tyrol Basin
- Cabin 857-1- Christmas Mountain Village
- Kalahari Indoor Water Park
- Mt. Olympus Parks, Parthenon Indoor Theme Park
- Henry Vilas Zoo
- Wild Rock Golf Club
- Lost World Water Park
- Alligator Alley
- Wollersheim Winery & Distillery
- Cascade Mountain
- Tom Foolerys Adventure Park
- Wild West water park
- Klondike Kavern Water Park
- University Ridge Golf Course
- Pirate's Cove Adventure Golf
- Baraboo Bluff Winery




